Agents for influencing plant growth

ABSTRACT

Agents for influencing plant growth, containing as active ingredient an azolylacetophenone oxime ether of the formula ##STR1## where R and R 1  independently of one another are each hydrogen, halogen, alkyl, cycloakyl, alkoxy, alkylthio, alkylsulfonyl, haloalkyl, nitro, cyano, phenyl or phenoxy, R 2  is hydrogen, alkyl, aralkyl, allyl or propargyl, R 3  is a divalent radical of the formula --(CH 2 ) m  --, --(CH 2  CH 2  O--) u  CH 2  CH 2  --, --(CH 2 ) v  CH═CH--(CH 2 ) t  -- or --(CH 2 ) v  --C.tbd.C--(CH 2 ) t  --, n, p, u, v and t independently of one another are each 1, 2 or 3, m is an integer from 2 to 10, and Az is 1,2,4-triazol-1-yl, pyrazol-1-yl or imidazol-1-yl, or a salt or metal complex thereof, and a method of influencing plant growth or of destroying unwanted plants with these active ingredients.

The present invention relates to agents which are based onazolylacetophenone oxime ethers and which influence the growth of plantsor act as herbicides.

It has been disclosed that azolylacetophenone oxime ethers can be usedas fungicides (German Laid-Open Application No. DOS 2,431,407).Bioregulator, plant growth regulator or herbicidal activity of suchoxime ethers is unknown to date.

We have found that azolylacetophenone oxime ethers of the formula (I)##STR2## where R and R¹ independently of one another are each hydrogen,halogen, alkyl, cycloalkyl, alkoxy, alkylthio, alkylsulfonyl, haloalkyl,nitro, cyano, unsubstituted or substituted phenyl or unsubstituted orsubstituted phenoxy, R² is hydrogen, alkyl, aralkyl or unsubstituted orsubstituted allyl or is propargyl, R³ is a divalent radical of theformula --(CH₂)_(m) --, --(CH₂ CH₂ O--)_(u) CH₂ CH₂ --, --(CH₂)_(v)--CH═CH--(CH₂)_(t) -- or --(CH₂)_(v) --C.tbd.C--(CH₂)_(t) --, n, p, u, vand t independently of one another are each 1, 2 or 3, m is an integerfrom 2 to 10, and Az is 1,2,4-triazol-1-yl, pyrazol-1-yl orimidazol-1-yl, and their salts and metal complexes can be usedsuccessfully as bioregulators, i.e. agents for influencing plant growth,in the widest sense.

The action can extend to modification of the form of growth of theplants, alteration of substances present in the plants, and destructionof undesirable plants.

In formula (I), R and R¹ independently of one another are each, forexample, halogen (fluorine, chlorine or bromine), nitro, cyano, alkyl oralkylsulfonyl, each of 1 to 4 carbon atoms, alkoxy or alkylthio, each of1 or 2 carbon atoms, haloalkyl of 1 to 4, in particular 1 or 2, carbonatoms, and 1 to 5 halogen atoms, in particular 1 to 3 identical ordifferent halogen atoms, preferred halogen atoms being fluorine andchlorine. Haloalkyl is particularly preferably trifluoromethyl.

R and R¹ independently of one another can furthermore be phenoxy orphenyl which is unsubstituted or, preferably, monosubstituted orpolysubstituted (disubstituted or trisubstituted) by identical ordifferent substituents, preferred substituents in each case beinghalogen, in particular fluorine, chlorine or bromine, cyano, nitro andhaloalkyl of 1 or 2 carbon atoms and not more than 3 identical ordifferent halogen atoms, preferred halogen atoms being fluorine andchlorine, and an example of haloalkyl being trifluoromethyl.

In formula (I), R² is preferably straight-chain or branched alkyl of 1to 5 carbon atoms, e.g. methyl, ethyl, n-propyl, isopropyl, sec.-butylor neopentyl. R² may furthermore be aralkyl where alkyl is of 1 to 4carbon atoms, unsubstituted phenyl being the preferred aryl. Examples ofaralkyl are thus benzyl, phenethyl, phenylpropyl and phenylbutyl. R² canalso be allyl which is unsubstituted or substituted by 1, 2 or 3chlorine atoms, or can be propargyl. Examples of allyl radicals areallyl, 2,3-dichloroallyl and 2,3,3-trichloroallyl.

In formula (I), R³ is a divalent radical of the formula --(CH₂)_(m) --,for example --CH₂ CH₂ --, --(CH₂)₃ --, --(CH₂)₄ --, --(CH₂)₅ --, (CH₂)₆--, (CH₂)₇ -- or --(CH₂)₈ --.

R³ can furthermore be a divalent radical containing one, two or threeoxygen atoms, of the formula --(CH₂ CH₂ O)_(u) CH₂ CH₂ --, for example--CH₂ CH₂ OCH₂ CH₂ --, --CH₂ CH₂ OCH₂ CH₂ OCH₂ CH₂ -- or --(CH₂ CH₂ O)₃CH₂ CH₂ --.

Finally, R³ can be a divalent radical which contains a double or triplebond and is of the formula --(CH₂)_(v) --CH═CH--(CH₂)_(t) or --(CH₂)_(v)--C.tbd.C--(CH₂)_(t) --.

Examples are --CH₂ --CH═CH--CH₂ --, --(CH₂)₂ --CH═CH--(CH₂)₂ --,--(CH₂)₃ --CH═CH--(CH₂)₃ --, --CH₂ --CH═CH--CH₂ --, --(CH₂)₂--C.tbd.C--(CH₂)₂ -- and --(CH₂)₃ --C═C--(CH₂)₃ --.

m is an integer from 2 to 10, preferably from 2 to 8.

If the agents are intended for use as growth regulators in the narrowersense, R, R¹, R², R³, m, n, p, u and Az preferably have the followingmeanings:

R and R¹ independently of another are each F, Cl, Br, C₁ -C₅ -alkyl,methoxy, ethoxy, methylthio, ethylthio, C₁ -C₃ -haloalkyl containing notmore than 4 fluorine or chlorine atoms, or unsubstituted or substitutedphenyl or phenoxy,

R² is hydrogen,

R³ is --(CH₂)_(m) --, --(CH₂ CH₂ O)_(u) --CH₂ CH₂ --, --CH₂ --CH═CH--CH₂-- or --CH₂ --C.tbd.C--CH₂ --,

n, p and u are each 1, 2 or 3,

m is from 2 to 8, and

Az is 1,2,4-triazol-1-yl, pyrazol-1-yl or imidazol-1-yl;

salts of the compounds can also be used.

Herbicidal agents are obtained in particular when R³ is a divalentradical --(CH₂)_(m) --, where m is 2, 3 or 4.

Examples of salts of the azolylacetophenone oxime ethers of the formula(I) are the hydrochlorides, hydrobromides, sulfates, phosphates andp-toluenesulfonates.

A metal complex is, for example, an adduct of one equivalent of a zincor copper salt, e.g. CuCl₂ or ZnCl₂, with two equivalents of a compound(I).

PREPARATION EXAMPLE2,4-Dichloro-ω-[1,2,4-triazol-1-yl]-acetophenoneoximeO-[2-(4-chlorophenoxy)ethyl] ether, E and Z isomers

23 g (0.085 mole) of 2,4-dichloro-ω-[1,2,4-triazol-1-yl]-acetophenoneoxime, 20 g of 2-[4-chlorophenoxy]-bromoethane, 7.1 g of powdered KOHand 5.8 g of triethylbenzylammonium chloride in 100 ml of toluene arestirred vigorously at 80°-100° C. for 1 hour. The mixture is evaporateddown, the residue is taken up in 250 ml of dichloromethane, the solutionis washed with three times 100 ml of water, and the organic phase isdried with sodium sulfate and evaporated down. Chromatography oversilica gel, using dichloromethane as eluant, gives 6 g of the Z isomer(active ingredient No. 23) and 4 g of the E isomer of2,4-dichloro-ω-[1,2,4-triazol-1-yl]-acetophenone oximeO-[2-(4-chlorophenoxy)-ethyl] ether (active ingredient No. 24). The Zisomer is the first to be eluted.

The compounds listed in the Table below can be prepared in a similarmanner. The configuration in which the oxime oxygen and the C aromaticring are on the same side of the oxime double bond is designated E,while the corresponding, other isomer is designated Z.

Tri=1,2,4-triazol-1-yl, Pyr=pyrazol-1-yl, Im=imidazolyl, Ts=tosyl,Bu=butyl and Me=methyl.

Those compounds of the formula I which are shown in the Table below andfor which melting points (mp.) or characteristics bands are given wereprepared in a similar manner. Their structures were confirmed byelemental analysis. The compounds for which no physicochemical data aregiven can be obtained in the manner described for the compounds actuallyprepared; because of their similar constitution, they are expected tohave actions similar to those of the compounds investigated in detail.

                                      TABLE A                                     __________________________________________________________________________    Compounds of the formula I with R.sup.3 = (CH.sub.2).sub.m:                    ##STR3##                                                                     No. R.sub.n R.sub.p.sup.1                                                                       R.sup.2 Az     Configuration                                                                        m  M.p. [°C.]                  __________________________________________________________________________    1   H       H     H       Tri    E/Z mixture                                                                          2                                     2   H       H     H       Tri    E/Z mixture                                                                          4  oil                                3   H       H     H       Tri    E/Z mixture                                                                          6                                     4   H       H     H       Tri    E/Z mixture                                                                          8                                     5   4-Cl    H     H       Tri    E/Z mixture                                                                          2  96-98                              6   4-Br    H     H       Tri    E/Z mixture                                                                          2  89-90                              7   4-OMe   H     H       Tri    E/Z mixture                                                                          2                                     8   4-CN    H     H       Tri    E/Z mixture                                                                          2                                     9   4-CF.sub.3                                                                            H     H       Tri    E/Z mixture                                                                          2                                     10  4-NO.sub.2                                                                            H     H       Tri    E/Z mixture                                                                          2                                     11  4-OC.sub.6 H.sub.5                                                                    H     H       Tri    E/Z mixture                                                                          2                                     12  2,4-Cl.sub.2                                                                          H     H       Tri.HNO.sub. 3                                                                       E/Z mixture                                                                          2  96                                 13  2,4-Cl.sub.2                                                                          H     H       Tri    Z      3  oil                                14  2,4-Cl.sub.2                                                                          H     H       Tri    E      3  oil                                15  2,4-Cl.sub.2                                                                          H     H       Tri    Z      4  oil                                16  2,4-Cl.sub.2                                                                          H     H       Tri    E      4  oil                                17  2,4-Cl.sub.2                                                                          H     H       Tri    Z      5  oil                                18  2,4-Cl.sub.2                                                                          H     H       Tri    E      5  oil                                19  2,4-Cl.sub.2                                                                          H     H       Tri    Z      6  oil                                20  2,4-Cl.sub.2                                                                          H     H       Tri    E      6  oil                                21  2,4-Cl.sub.2                                                                          H     H       Tri    E      8                                     22  2,4-Cl.sub.2                                                                          H     H       Tri    E      8                                     23  2,4-Cl.sub.2                                                                          4-Cl  H       Tri    Z      2  87-91                              24  2,4-Cl.sub.2                                                                          4-Cl  H       Tri    E      2  58-61                              25  2,4-Cl.sub.2                                                                          4-Cl  H       Tri.HNO.sub.3                                                                        E/Z mixture                                                                          2                                     26  2,4-Cl.sub.2                                                                          4-Cl  H       Tri.HNO.sub.3                                                                        E/Z mixture                                                                          2                                     27  2,4-Cl.sub.2                                                                          4-Cl  H       Tri.H.sub.2 SO.sub.4                                                                 E/Z mixture                                                                          2                                     28  2,4-Cl.sub.2                                                                          4-Cl  H       Tri.H.sub.3 PO.sub.4                                                                 E/Z mixture                                                                          2                                     29  2,4-Cl.sub.2                                                                          4-Cl  H       Tri.TsOH                                                                             E/Z mixture                                                                          2                                     30  2,4-Cl.sub.2                                                                          4-Cl  H       Tri.1/2 CuCl.sub.2                                                                   E/Z mixture                                                                          2                                     31  2,4-Cl.sub.2                                                                          4-Cl  H       Tri.1/2 ZnCl.sub.2                                                                   E/Z mixture                                                                          2                                     32  2,4-Cl.sub.2                                                                          4-Cl  CH.sub.3                                                                              Tri    E/Z mixture                                                                          2                                     33  2,4-Cl.sub.2                                                                          4-Cl  n-Bu    Tri    E/Z mixture                                                                          2                                     34  2,4-Cl.sub.2                                                                          4-Cl  CH.sub.2 C.sub.6 H.sub.5                                                              Tri    E/Z mixture                                                                          2                                     35  2,4-Cl.sub.2                                                                          4-Cl  CH.sub.2 C(CH.sub.3).sub.3                                                            Tri    E/Z mixture                                                                          2                                     36  2,4-Cl.sub.2                                                                          4-Cl  H       Tri    Z      3  oil                                37  2,4-Cl.sub.2                                                                          4-Cl  H       Tri    E      3  oil                                38  2,4-Cl.sub.2                                                                          4-Cl  H       Tri    Z      4  65-71                              39  2,4-Cl.sub.2                                                                          4-Cl  H       Tri    E      4  oil                                40  2,4-Cl.sub.2                                                                          4-Cl  H       Tri    Z      5  oil                                41  2,4-Cl.sub.2                                                                          4-Cl  H       Tri    E      5  59-62                              42  2,4-Cl.sub.2                                                                          2,4-Cl.sub.2                                                                        H       Tri    Z      2   95-100                            43  2,4-Cl.sub.2                                                                          2,4-Cl.sub.2                                                                        H       Tri    E      2  oil                                44  2,4-Cl.sub.2                                                                          2,4-Cl.sub.2                                                                        CH.sub.3                                                                              Tri    E/Z mixture                                                                          2                                     45  2,4-Cl.sub.2                                                                          2,4-Cl.sub.2                                                                        n-Bu    Tri    E/Z mixture                                                                          2                                     46  2,4-Cl.sub.2                                                                          2,4-Cl.sub.2                                                                        CH.sub.2C.sub.6 H.sub.5                                                               Tri    E/Z mixture                                                                          2                                     47  2,4-Cl.sub.2                                                                          2,4-Cl.sub.2                                                                        CH.sub.2C(CH.sub.3)                                                                   Tri    E/Z mixture                                                                          2                                     48  2,4-Cl.sub.2                                                                          2,4-Cl.sub.2                                                                        H       Tri.HNO.sub.3                                                                        E/Z mixture                                                                          2  132 (decomposition)                49  2,4-Cl.sub.2                                                                          2,4,6-Cl.sub.3                                                                      H       Tri.HCl                                                                              E/Z mixture                                                                          2                                     50  2,4-Cl.sub.2                                                                          2,4,6-Cl.sub.3                                                                      H       Tri.1/2 ZnCl.sub.2                                                                   E/Z mixture                                                                          2                                     51  2,4-Cl.sub.2                                                                          2,4,6-Cl.sub.3                                                                      H       Tri.1/2 CuCl.sub.2                                                                   E/Z mixture                                                                          2                                     52  2,4-Cl.sub.2                                                                          4-F   H       Tri    Z      2  66-70                              53  2,4-Cl.sub.2                                                                          4-F   H       Tri    E      2  73-77                              54  2,4-Cl.sub.2                                                                          4-CN  H       Tri    Z      2   96-100                            55  2,4-Cl.sub.2                                                                          4-CN  H       Tri    E      2                                     56  2,4-Cl.sub.2                                                                          4-tert.-Bu                                                                          H       Tri.HNO.sub.3                                                                        E/Z mixture                                                                          2  117                                57  2,4-Cl.sub.2                                                                          4-OMe H       Tri    Z      2  oil                                58  2,4-Cl.sub.2                                                                          4-OMe H       Tri    E      2                                     59  2,4-Cl.sub.2                                                                          4-SMe H       Tri    E/Z mixture                                                                          2                                     60  2,4-Cl.sub.2                                                                          4-Br  H       Tri    E/Z mixture                                                                          2                                     61  2,4-Cl.sub.2                                                                          4-NO.sub.2                                                                          H       Tri    E/Z mixture                                                                          2                                     62  2,4-Cl.sub.2                                                                          3-Cl  H       Tri    Z      2  oil                                63  2,4-Cl.sub.2                                                                          3-Cl  H       Tri    E      2  73-77                              64  2,4-Cl.sub.2                                                                          3-CF.sub.3                                                                          H       Tri    Z      2  oil                                65  2,4-Cl.sub.2                                                                          3-CF.sub.3                                                                          H       Tri    E      2  66-69                              66  2,4-Cl.sub.2                                                                          4-Cl  CH.sub.2 HCCH.sub.2                                                                   Tri    E/Z mixture                                                                          2                                     67  2,4-Cl.sub.2                                                                          4-Cl  CH.sub.2 CClCCl.sub.2                                                                 Tri    E/Z mixture                                                                          2                                     68  2,4-Cl.sub.2                                                                          4-Cl  propargyl                                                                             Tri    E/Z mixture                                                                          2                                     69  2,4-Cl.sub.2 -3-CH.sub.3                                                              4-Cl  H       Tri    E/Z mixture                                                                          2  oil                                70  2,5-Cl.sub.2                                                                          4-Cl  H       Tri    Z      2  oil                                71  2,5-Cl.sub.2                                                                          H     H       Tri    E      2  82-86                              72  2,4-Cl.sub.2                                                                          H     H       Pyr    E/Z mixture                                                                          2                                     73  2,4-Cl.sub.2                                                                          H     H       Pyr    E/Z mixture                                                                          3                                     74  2,4-Cl.sub.2                                                                          H     H       Pyr    E/Z mixture                                                                          4                                     75  2,4-Cl.sub.2                                                                          H     H       Pyr    E/Z mixture                                                                          5                                     76  2,4-Cl.sub.2                                                                          4-Cl  H       Pyr    E/Z mixture                                                                          2                                     77  2,4-Cl.sub.2                                                                          4-F   H       Pyr    E/Z mixture                                                                          2                                     78  2,4-Cl.sub.2                                                                          4-CN  H       Pyr    E/Z mixture                                                                          2                                     79  2,4-Cl.sub.2                                                                          4-OMe H       Pyr    E/Z mixture                                                                          2                                     80  2,4-Cl.sub.2                                                                          4-Cl  CH.sub.3                                                                              Pyr    E/Z mixture                                                                          2                                     114 2,4-Cl.sub.2                                                                          2,4,6-Cl.sub.3                                                                      H       Tri    Z isomer                                                                             2  76-85                              127 4-Cl    2,4,6-Cl.sub.3                                                                      H       Tri    Z isomer                                                                             2  114-116                            128 H       4-Cl  H       Tri    Z isomer                                                                             2  79-83                              129 H       4-Cl  H       Tri    Z isomer                                                                             3  59-64                              130 H       4-Cl  H       Tri    Z isomer                                                                             4  59-62                              131 H       3-Cl  H       Tri    Z isomer                                                                             2  73-75                              132 H       3-CH.sub.3                                                                          H       Tri    Z isomer                                                                             2  54-56                              133 H       H     H       Tri.1/2 CuCl.sub.2                                                                   E/Z mixture                                                                          4  wax-like                           134 H       H     H       Tri.HCl                                                                              E/Z mixture                                                                          4  wax-like                           135 H       H     H       Tri    E/Z mixture                                                                          4  oil                                136 H       4-Cl  H       Tri.1/2 CuCl.sub.2.                                                                  E/Z mixture                                                                          4  wax-like                           137 H       4-Cl  H       Tri.HCl                                                                              E/Z mixture                                                                          4  108-115                            138 H       4-Cl  H       Tri    E/Z mixture                                                                          4  oil                                139 H       4-Cl  H       Tri.1/2 CuCl.sub.2                                                                   E/Z mixture                                                                          2  wax-like                           140 H       4-Cl  H       Tri.HCl                                                                              E/Z mixture                                                                          2  138-142                            141 H       4-Cl  H       Tri    E/Z mixture                                                                          2  oil                                142 H       3-Cl  H       Tri    E/Z mixture                                                                          2  oil                                143 H       3-Cl  H       Tri.HCl                                                                              E/Z mixture                                                                          2  wax-like                           144 H       3-Cl  H       Tri.1/2 CuCl.sub.2                                                                   E/Z mixture                                                                          2  wax-like                           145 H       3-CH.sub.3                                                                          H       Tri    E/Z mixture                                                                          2  oil                                146 H       3-CH.sub.3                                                                          H       Tri.HCl                                                                              E/Z mixture                                                                          2  wax-like                           147 H       3-CH.sub.3                                                                          H       Tri.1/2 CuCl.sub.2                                                                   E/Z mixture                                                                          2  wax-like                           148 4-CH.sub.3                                                                            4-Cl  H       Tri    Z isomer                                                                             2  110-112                            149 4-CH.sub.3                                                                            4-Cl  H       Tri.HCl                                                                              Z isomer                                                                             2  164-167                            150 4-CH.sub.3                                                                            3-Cl  H       Tri    Z isomer                                                                             2  86-91                              151 4-CH.sub.3                                                                            3-Cl  H       Tri.HCl                                                                              Z isomer                                                                             2  oil                                152 4-CH.sub.3                                                                            3-CH.sub.3                                                                          H       Tri    Z isomer                                                                             2  66-71                              153 4-CH.sub.3                                                                            3-CH.sub.3                                                                          H       Tri.HCl                                                                              Z isomer                                                                             2  125-128                            154 4-CH.sub.3                                                                            4-Cl  H       Tri    Z isomer                                                                             3  70-72                              155 4-CH.sub.3                                                                            4-Cl  H       Tri.HCl                                                                              Z isomer                                                                             3  160-163                            156 4-CH.sub.3                                                                            H     H       Tri    Z isomer                                                                             4  58-61                              157 4-CH.sub.3                                                                            H     H       Tri.HCl                                                                              Z isomer                                                                             4  120-124                            158 4-CH.sub.3                                                                            4-Cl  H       Tri    Z isomer                                                                             4  75-76                              159 4-CH.sub.3                                                                            4-Cl  H       Tri.HCl                                                                              Z isomer                                                                             4  123-125                            160 4-Cl    4-Cl  H       Tri    Z isomer                                                                             2  133-135                            161 4-Cl    4-Cl  H       Tri.HCl                                                                              Z isomer                                                                             2  174-178                            162 4-Cl    4-Cl  H       Tri    Z isomer                                                                             4  75-81                              163 4-Cl    4-Cl  H       Tri.HCl                                                                              Z isomer                                                                             4  128-130                            164 4-Cl    H     H       Tri    Z isomer                                                                             4  51-56                              165 4-Cl    H     H       Tri.HCl                                                                              Z isomer                                                                             4  136                                166 4-Cl    3-Cl  H       Tri    Z isomer                                                                             2  89-94                              167 4-Cl    3-Cl  H       Tri.HCl                                                                              Z isomer                                                                             2  141-145                            168 4-Cl    3-CH.sub.3                                                                          H       Tri    Z isomer                                                                             2  103-105                            169 4-Cl    3-CH.sub.3                                                                          H       Tri.HCl                                                                              Z isomer                                                                             2  107-108                            179 4-Cl    3-CF.sub.3                                                                          H       Tri           2  89-93                              180 4-Cl    3,5-Cl.sub.2                                                                        H       Tri           2  88-94                              181 4-CH.sub.3                                                                            3,5-Cl.sub.2                                                                        H       Tri           2  70-74                              182 4-Cl    3-Cl  H       Tri           3  67-69                              183 4-CH.sub.3                                                                            3-Cl  H       Tri           2  54-57                              184 4-Cl    3-Cl  H       Im            2  119-123                            185 4-Cl    3-Cl  H       Pyr           2  73-78                              186 H       3-Cl  H       Im            2                                     187 H       3-Cl  H       Pyr           2  oil                                188 4-Cl    3,4-Cl.sub.2                                                                        H       Tri    Z isomer                                                                             2  83                                 189 4-Cl    2,3-Cl.sub.2                                                                        H       Tri    Z isomer                                                                             2  103-106                            190 4-Cl    3-OCH.sub.3                                                                         H       Tri    Z isomer                                                                             2  99                                 191 3,4-Cl.sub.2                                                                          3-Cl  H       Tri    Z isomer                                                                             2  84                                 192 4-F     3-Cl  H       Tri    Z isomer                                                                             2  71-74                              193 3,4-Cl.sub.2                                                                          3-CH.sub.3                                                                          H       Tri    Z isomer                                                                             2  73-75                              194 4-F     3-CH.sub.3                                                                          H       Tri    Z isomer                                                                             2  63-65                              195 4-Cl    3-NO.sub.2                                                                          H       Tri    Z isomer                                                                             2  135-137                            196 4-C.sub.6 H.sub.5                                                                     3-Cl  H       Tri    Z/E mixture                                                                          2  60-63                              197 4-C.sub.6 H.sub.5                                                                     3-CH.sub.3                                                                          H       Tri    Z/E mixture                                                                          2  wax-like                           198 4-Cl    2,4,5-Cl.sub.3                                                                      H       Tri    Z/E mixture                                                                          2  89                                 199 4-Cl    2,5-Cl.sub.2                                                                        H       Tri    Z/E mixture                                                                          2  124-126                            200 4-OCH.sub.3                                                                           3-CF.sub.3                                                                          H       Tri    Z/E mixture                                                                          2  64-67                              201 4-C.sub.6 H.sub.5                                                                     3-CF.sub.3                                                                          H       Tri    Z/E mixture                                                                          2  87-90                              202 4-F     3-CF.sub.3                                                                          H       Tri    Z/E mixture                                                                          2  70-74                              203 3,4-Cl.sub.2                                                                          3-CF.sub.3                                                                          H       Tri    Z/E mixture                                                                          2  90-94                              204 4-OCH.sub.3                                                                           3-Cl  H       Tri    Z/E mixture                                                                          2  48-50                              205 4-OCH.sub.3                                                                           3-CH.sub.3                                                                          H       Tri    Z/E mixture                                                                          2  oil                                206 H       3-CH.sub.3                                                                          H       Tri    Z/E mixture                                                                          2                                     207 4-(CH.sub.3).sub.2 CH                                                                 3-Cl  H       Tri    Z/E mixture                                                                          2                                     208 4-(CH.sub.3).sub.2 CH                                                                 3-CH.sub.3                                                                          H       Tri    Z/E mixture                                                                          2                                     209 4-(CH.sub.3).sub.2 CH                                                                 3,4-Cl.sub.2                                                                        H       Tri    Z/E mixture                                                                          2                                     210 4-(CH.sub.3).sub.2 CH                                                                 2,3-Cl.sub.2                                                                        H       Tri    Z/E mixture                                                                          2                                     211 4-(CH.sub.3).sub.2 C                                                                  3-CH.sub.3                                                                          H       Tri    Z/E mixture                                                                          2                                     212 4-(CH.sub.3).sub.2 C                                                                  3-Cl  H       Tri    Z/E mixture                                                                          2                                     213 4-(CH.sub.3).sub.3 C                                                                  3,4-Cl.sub.2                                                                        H       Tri    Z/E mixture                                                                          2                                     214 4-(CH.sub.3).sub.3 C                                                                  2,3-Cl.sub.2                                                                        H       Tri    Z/E mixture                                                                          2                                     215 4-cycl.-C.sub.6 H.sub.11                                                              3-CH.sub.3                                                                          H       Tri    Z/E mixture                                                                          2                                     216 4-cycl.-C.sub.6 H.sub.11                                                              3-Cl  H       Tri    Z/E mixture                                                                          2                                     217 4-cycl.-C.sub.6 H.sub.11                                                              3,4-Cl.sub.2                                                                        H       Tri    Z/E mixture                                                                          2                                     218 4-cycl.-C.sub.6 H.sub.11                                                              2,3-Cl.sub.2                                                                        H       Tri    Z/E mixture                                                                          2                                     219 4-C.sub.6 H.sub.5                                                                     2,3-Cl.sub.2                                                                        H       Tri    Z/E mixture                                                                          2                                     220 4-C.sub.6 H.sub.5                                                                     2,3-Cl.sub.2                                                                        H       Tri    Z/E mixture                                                                          2                                     221 4-OCH.sub.3                                                                           2,3-Cl.sub.2                                                                        H       Tri    Z/E mixture                                                                          2                                     222 4-OCH.sub.3                                                                           3,4-Cl.sub.2                                                                        H       Tri    Z/E mixture                                                                          2                                     223 4-OC.sub.6 H.sub.5                                                                    3-Cl  H       Tri    Z/E mixture                                                                          2                                     224 4-OC.sub.6 H.sub.5                                                                    3-OCH.sub.3                                                                         H       Tri    Z/E mixture                                                                          2                                     225 4-OC.sub.6 H.sub.5                                                                    2,3-Cl.sub.2                                                                        H       Tri    Z/E mixture                                                                          2                                     226 4-OC.sub.6 H.sub.5                                                                    3,4-Cl.sub.2                                                                        H       Tri    Z/E mixture                                                                          2                                     237 4-NO.sub.2                                                                            3-Cl  H       Tri    Z/E mixture                                                                          2                                     238 4-NO.sub.2                                                                            3-CH.sub.3                                                                          H       Tri    Z/E mixture                                                                          2                                     239 4-NO.sub.2                                                                            3,4-Cl.sub.2                                                                        H       Tri    Z/E mixture                                                                          2                                     240 4-NO.sub.2                                                                            2,3-Cl.sub.2                                                                        H       Tri    Z/E mixture                                                                          2                                     241 2-Cl    3-Cl  H       Tri    Z/E mixture                                                                          2                                     242 2-Cl    3-CH.sub.3                                                                          H       Tri    Z/E mixture                                                                          2                                     243 2-Cl    2,3-Cl.sub.2                                                                        H       Tri    Z/E mixture                                                                          2                                     244 2-Cl    3,4-Cl.sub.2                                                                        H       Tri    Z/E mixture                                                                          2                                     245 3,5-Cl.sub.2                                                                          3-Cl  H       Tri    Z/E mixture                                                                          2                                     246 3,5-Cl.sub.2                                                                          3-CH.sub.3                                                                          H       Tri    Z/E mixture                                                                          2                                     247 4-Br    3-Cl  H       Tri    Z/E mixture                                                                          2                                     248 4-Br    3-CH.sub.3                                                                          H       Tri    Z/E mixture                                                                          2                                     249 H       3-Cl  CH.sub.3                                                                              Tri    Z/E mixture                                                                          2                                     250 H       3-CH.sub.3                                                                          CH.sub.3                                                                              Tri    Z/E mixture                                                                          2                                     251 H       3-Cl  CH.sub.2 CH.sub.3                                                                     Tri    Z/E mixture                                                                          2                                     252 H       3-CH.sub.3                                                                          CH.sub.2 CH.sub.3                                                                     Tri    Z/E mixture                                                                          2                                     253 H       3-Cl  CH.sub.2 CH.sub.2 CH.sub.3                                                            Tri    Z/E mixture                                                                          2                                     254 H       3-CH.sub.3                                                                          CH.sub.2 CH.sub.2 CH.sub.3                                                            Tri    Z/E mixture                                                                          2                                     255 4-F     3-F   H       Tri    Z/E mixture                                                                          2                                     256 H       2-F   H       Tri    Z      2                                     257 H       2-F   H       Tri    E      2                                     258 H       2-Cl  H       Tri    Z      2                                     259 H       2-Cl  H       Tri    E      2                                     260 4-CH.sub.3                                                                            2-F   H       Tri    Z      2                                     261 4-CH.sub.3                                                                            2-F   H       Tri    E      2                                     262 4-CH.sub.3                                                                            2-Cl  H       Tri    Z      2                                     263 4-CH.sub.3                                                                            2-Cl  H       Tri    E      2                                     264 4-cycl.C.sub.6 H.sub.11                                                               2-F   H       Tri    Z      2                                     265 4-cycl.C.sub.6 H.sub.11                                                               2-F   H       Tri    E      2  77-80                              266 4-cycl.C.sub.6 H.sub.11                                                               2-Cl  H       Tri    Z      2                                     267 4-cycl.C.sub.6 H.sub.11                                                               2-Cl  H       Tri    E      2  wax-like                           268 4-C.sub.6 H.sub.5                                                                     2-F   H       Tri    Z      2  111                                269 4-C.sub.6 H.sub.5                                                                     2-F   H       Tri    E      2                                     270 4-C.sub.6 H.sub.5                                                                     2-Cl  H       Tri    Z      2  108                                271 4-C.sub.6 H.sub.5                                                                     2-Cl  H       Tri    E      2                                     272 4-Cl    2-F   H       Tri    Z      2                                     273 4-Cl    2-F   H       Tri    E      2                                     274 4-Cl    2-Cl  H       Tri    Z      2                                     275 4-Cl    2-Cl  H       Tri    E      2                                     276 4-F     2-Cl  H       Tri    E/Z mixture                                                                          2  74-77                              277 4-F     2-Cl  H       Tri    Z      2  81                                 278 4-F     2-Cl  H       Tri    E      2                                     279 4-F     2-F   H       Tri    Z      2  86                                 280 4-F     2-F   H       Tri    E      2                                     281 4-OCH.sub.3                                                                           2-F   H       Tri    Z      2  79-81                              282 4-OCH.sub.3                                                                           2-F   H       Tri    E      2                                     283 4-OCH.sub.3                                                                           2-Cl  H       Tri    Z      2  71                                 284 4-OCH.sub.3                                                                           2-Cl  H       Tri    E      2                                     285 4-CN    2-F   H       Tri    Z      2                                     286 4-CN    2-F   H       Tri    E      2                                     287 H       2-CN  H       Tri    Z      2                                     288 H       2-CN  H       Tri    E      2                                     289 4-CH.sub.3                                                                            2-CN  H       Tri    Z      2                                     290 4-CH.sub.3                                                                            2-CN  H       Tri    E      2                                     291 4-Cl    2-CN  H       Tri    Z      2                                     292 4-Cl    2-CN  H       Tri    E      2                                     293 4-F     2-CN  H       Tri    Z      2                                     294 4-F     2-CN  H       Tri    E      2                                     295 H       2-CH.sub.3                                                                          H       Tri    Z      2                                     296 H       2-CH.sub.3                                                                          H       Tri    E      2                                     297 4-CH.sub.3                                                                            2-CH.sub.3                                                                          H       Tri    Z      2                                     298 4-CH.sub.3                                                                            2-CH.sub.3                                                                          H       Tri    E      2                                     299 4-Cl    2-CH.sub.3                                                                          H       Tri    Z      2                                     300 4-Cl    2-CH.sub.3                                                                          H       Tri    E      2                                     301 4-F     2-CH.sub.3                                                                          H       Tri    Z      2                                     302 4-F     2-CH.sub.3                                                                          H       Tri    E      2                                     303 H       2-OCH.sub.3                                                                         H       Tri    Z      2                                     304 H       2-OCH.sub.3                                                                         H       Tri    E      2                                     305 2-CH.sub.3                                                                            2-OCH.sub.3                                                                         H       Tri    Z      2                                     306 2-CH.sub.3                                                                            2-OCH.sub.3                                                                         H       Tri    E      2                                     307 2-Cl    2-OCH.sub.3                                                                         H       Tri    Z      2                                     308 2-Cl    2-OCH.sub.3                                                                         H       Tri    E      2                                     309 2-F     2-OCH.sub.3                                                                         H       Tri    Z      2                                     310 2-F     2-OCH.sub.3                                                                         H       Tri    E      2                                     311 3-Cl    2-Cl  H       Tri    Z      2                                     312 3-Cl    2-F   H       Tri    Z      2                                     313 3-Br    2-Cl  H       Tri    Z      2                                     314 3,4-Cl.sub.2                                                                          2-Cl  H       Tri    Z      2  98                                 315 3,4-Cl.sub.2                                                                          2-F   H       Tri    Z      2  103-105                            316 3,5-Cl.sub.2                                                                          2-F   H       Tri    Z      2  117                                317 3,5-Cl.sub.2                                                                          2-Cl  H       Tri    Z      2  108                                318 2,5-Cl.sub.2                                                                          2-F   H       Tri.HNO.sub.3                                                                        Z      2  110                                319 2,5-Cl.sub.2                                                                          2-Cl  H       Tri    Z      2  wax-like                           320 2,4-Cl.sub.2                                                                          2-F   H       Tri    Z      2                                     321 2,4-Cl.sub.2                                                                          2-Cl  H       Tri    Z      2                                     322 2-Cl    2-F   H       Tri    Z      2                                     323 2-Cl    2-Cl  H       Tri    Z      2                                     324 H       2,6-Cl.sub.2                                                                        H       Tri    Z      2                                     325 4-CH.sub.3                                                                            2,6-Cl.sub.2                                                                        H       Tri    Z      2                                     326 4-Cl    2,6-Cl.sub.2                                                                        H       Tri    Z      2                                     327 4-F     2,6-Cl.sub.2                                                                        H       Tri    Z      2                                     328 2,5-Cl.sub.2                                                                          3-Cl  H       Tri    Z      2  oil                                329 3-Br    3-Cl  H       Tri    Z      2  100-103                            __________________________________________________________________________

                  TABLE B                                                         ______________________________________                                        Compounds of the formula I with R.sup.3 = (CH.sub.2 CH.sub.2 O).sub.u         CH.sub.2 CH.sub.2                                                              ##STR4##                                                                                                                 M.p.                              No.  R.sub.n R.sub.p.sup.1                                                                          R.sup.2                                                                           Az   Configuration                                                                          m   [°C.]                      ______________________________________                                         81  2,4-Cl.sub.2                                                                          H        H   Tri  E/Z mixture                                                                            1                                      82  2,4-Cl.sub.2                                                                          H        H   Tri  E/Z mixture                                                                            2   oil                                83  2,4-Cl.sub.2                                                                          H        H   Tri  E/Z mixture                                                                            3                                      84  2,4-Cl.sub.2                                                                          4-Cl     H   Tri  E/Z mixture                                                                            1                                      85  2,4-Cl.sub.2                                                                          4-Cl     H   Tri  E/Z mixture                                                                            2   oil                                86  2,4-Cl.sub.2                                                                          4-Cl     H   Tri  E/Z mixture                                                                            3                                      87  2,4-Cl.sub.2                                                                          2,4-Cl.sub.2                                                                           H   Tri  E/Z mixture                                                                            1                                      88  2,4-Cl.sub.2                                                                          2,4-Cl.sub.2                                                                           H   Tri  E/Z mixture                                                                            2   oil                                89  2,4-Cl.sub.2                                                                          2,4-Cl.sub.2                                                                           H   Tri  E/Z mixture                                                                            3                                     106  2,4-Cl.sub.2                                                                          2-Cl     H   Tri  E/Z mixture                                                                            2   oil                               107  2,4-Cl.sub.2                                                                          3-Cl     H   Tri  E/Z mixture                                                                            2   oil                               108  2,4-Cl.sub.2                                                                          4-OCH.sub.3                                                                            H   Tri  Z isomer 2   oil                               109  2,4-Cl.sub.2                                                                          2,4,6-Cl.sub.3                                                                         H   Tri  Z isomer 2   oil                               110  2,4-Cl.sub.2                                                                          2-Cl     H   Tri  E/Z mixture                                                                            1   wax-like                          111  2,4-Cl.sub.2                                                                          4-OCH.sub.3                                                                            H   Tri  Z isomer 1   wax-like                          112  2,4-Cl.sub.2                                                                          3-CH.sub.3                                                                             H   Tri  Z isomer 1   wax-like                          113  2,4-Cl.sub.2                                                                          4-CH.sub.3                                                                             H   Tri  Z isomer 1   wax-like                          116  4-Cl    2,4,6-Cl.sub.3                                                                         H   Tri  Z isomer 1   69-71                             117  4-Cl    2-Cl     H   Tri  Z isomer 1   63-65                             118  4-Cl    3-CH.sub.3                                                                             H   Tri  Z isomer 1   66-68                             119  4-Cl    4-OCH.sub.3                                                                            H   Tri  Z isomer 1   71                                120  4-Cl    4-CH.sub.3                                                                             H   Tri  Z isomer 1   79                                121  4-Cl    H        H   Tri  Z isomer 2   oil                               122  4-Cl    4-Cl     H   Tri  Z isomer 2   85-88                             123  4-Cl    2-Cl     H   Tri  Z isomer 2   oil                               124  4-Cl    3-Cl     H   Tri  Z isomer 2   oil                               125  4-Cl    2,4-Cl.sub.2                                                                           H   Tri  Z isomer 2   48-53                             126  4-Cl    4-OCH.sub. 3                                                                           H   Tri  Z isomer 2   oil                               170  4-CH.sub.3                                                                            4-Cl     H   Tri  Z isomer 2   oil                               171  H       4-Cl     H   Tri  Z isomer 2   oil                               ______________________________________                                    

                  TABLE C                                                         ______________________________________                                        Compounds of the formula I with R.sup.3 =                                     (CH.sub.2).sub.vCHCH(CH.sub.2).sub.t                                           ##STR5##                                                                                                                     M.p.                          No.  R.sub.n R.sub.p.sup.1                                                                          R.sup.2                                                                           Az   Configuration                                                                          v   t   [°C.]                  ______________________________________                                        90   2,4-Cl.sub.2                                                                          4        H   Tri  E/Z mixture                                                                            1   1   oil                           91   2,4-Cl.sub.2                                                                          4-Cl     H   Tri  E/Z mixture                                                                            1   1   oil                           92   2,4-Cl.sub.2                                                                          4-CH.sub.3                                                                             H   Tri  E/Z mixture                                                                            1   1                                 93   2,4-Cl.sub.2                                                                          4-OCH.sub.3                                                                            H   Tri  E/Z mixture                                                                            1   1                                 94   2,4-Cl.sub.2                                                                          2,4-Cl.sub.2                                                                           H   Tri  E/Z mixture                                                                            1   1   oil                           95   2,4-Cl.sub.2                                                                          2,4,6-Cl.sub.2                                                                         H   Tri  E/Z mixture                                                                            1   1   oil                           96   2,4-Cl.sub.2                                                                          4-Cl     H   Tri  E/Z mixture                                                                            2   2                                 97   2,4-Cl.sub.2                                                                          4-Cl     H   Tri  E/Z mixture                                                                            3   3                                 115  2,4-Cl.sub.2                                                                          2-Cl     H   Tri  E/Z mixture                                                                            1   1   84                            ______________________________________                                    

                                      TABLE D                                     __________________________________________________________________________    Compounds of the formula I with R.sup.3 = (CH.sub.2).sub.vCC(CH.sub.2).sub    .t                                                                             ##STR6##                                                                     No.                                                                              R.sub.n                                                                            R.sub.p.sup.1                                                                       R.sup.2                                                                          Az  Configuration                                                                        v  t   M.p. [°C.]                          __________________________________________________________________________     98                                                                              2,4-Cl.sub.2                                                                       H     H  Tri E/Z mixture                                                                          1  1  oil                                          99                                                                              2,4-Cl.sub.2                                                                       4-Cl  H  Tri E/Z mixture                                                                          1  1  oil                                         100                                                                              2,4-Cl.sub.2                                                                       4-CH.sub.3                                                                          H  Tri E/Z mixture                                                                          1  1  oil                                         101                                                                              2,4-Cl.sub.2                                                                       4-OCH.sub.3                                                                         H  Tri E/Z mixture                                                                          1  1  oil                                         102                                                                              2,4-Cl.sub.2                                                                       2,4-Cl.sub.2                                                                        H  Tri E/Z mixture                                                                          1  1  oil                                         103                                                                              2,4-Cl.sub.2                                                                       3-CH.sub.3                                                                          H  Tri E/Z mixture                                                                          1  1  oil                                         104                                                                              2,4-Cl.sub.2                                                                       4-Cl  H  Tri E/Z mixture                                                                          2  2                                              105                                                                              2,4-Cl.sub.2                                                                       4-Cl  H  Tri E/Z mixture                                                                          3  3                                              172                                                                              2,4-Cl.sub.2                                                                       4-F   H  Tri Z isomer                                                                             1  1  oil                                         173                                                                              2,4-Cl.sub.2                                                                       3-Cl  H  Tri Z isomer                                                                             1  1  oil                                         174                                                                              4-Cl H     H  Tri Z isomer                                                                             1  1  70-75                                       175                                                                              4-Cl 4-Cl  H  Tri Z isomer                                                                             1  1  81-85                                       176                                                                              4-Cl 4-F   H  Tri Z isomer                                                                             1  1  70-75                                       177                                                                              4-Cl 3-Cl  H  Tri Z isomer                                                                             1  1  80-85                                       178                                                                              4-Cl 4-OCH.sub.3                                                                         H  Tri Z isomer                                                                             1  1  oil                                         __________________________________________________________________________

    ______________________________________                                        Characteristic NMR data (.sup.1 H-NMR):                                       No.   δ in ppm, solvent CDCl.sub.3                                      ______________________________________                                        13    4.05 "t" 2H; 4.45 "t" 2H; 5.39 s 2H, 7.72 s 1H;                               7.98 s 1H                                                               14    3.90 "t" 2H; 4.25 "t" 2H; 5.10 s 2H; 7.82 s 1H;                               7.90 s 1H                                                               15    4.00 "t" 2H; 4.35 "t" 2H; 5.40 s 2H; 7.80 s 1H;                               8.07 s 1H                                                               16    3.90 "t" 2H; 4.20 "t" 2H; 5.20 s 2H; 7.90 s 1H;                               8.00 s 1H                                                               17    4.00 "t" 2H; 4.30 "t" 2H; 5.44 s 2H; 7.82 s 1H;                               8.10 s 1H                                                               18    3.90 "t" 2H; 4.20 "t" 2H; 5.20 s 2H; 7.93 s 1H;                               8.04 s 1H                                                               36    4.03 "t" 2H; 4.43 "t" 2H; 5.44 s 2H; 7.80 s 1H;                               8.07 s 1H                                                               37    3.90 "t" 2H; 4.27 "t" 2H; 5.20 s 2H; 7.90 s 1H;                               8.00 s 1H                                                               39    3.78 "t" 2H; 4.08 "t"  2H; 5.05 s 2H; 7.70 s 1H;                              7.85 s 1H                                                               40    3.38 "t" 2H; 4.20 "t" 2H; 5.35 s 2H; 7.70 s 1H;                               7.98 s 1H                                                               43    4.22 "t" 2H; 4.48 "t" 2H; 5.23 s 2H; 7.98 s 1H;                               8.03 s 1H                                                               57    4.25 "t" 2H; 4.60 "t" 2H; 5.47 s 2H; 7.80 s 1H;                               8.17 s 1H                                                               62    4.27 "t" 2H; 4.60 "t" 2H; 5.48 s 2H; 7.80 s 1H;                               8.15 s 1H                                                               64    4.43 "t" 2H; 4.63 "t" 2H; 5.45 s 2H; 7.80 s 1H;                               8.13 s 1H                                                               69    2.41 3H; 4.22 "t" 2H; 4.58 "t" 2H; 5.41 s 2H;                                 7.78 s 1H; 8.11 s 1H                                                    70    4.22 "t" 2H; 4.59 "t" 2H; 5.42 s 2H; 7.81 s 1H;                               8.14 s 1H                                                               98    4.78 s 4H; 5.22 s 2H; 7.93 s 1H; 8.03 s 1H                              100   2.28 s 3H; 4.70 m 3H; 5.20 s 2H; 7.90 s 1H;                                   8.00 s 1H                                                               101   3.72 s 3H; 4.70 s 2H; 4.87 s 2H; 5.44 s 2H;                                   7.80 s 1H; 8.11 s 1H                                                    102   4.70 m 4H; 5.20 s and 5.50 s 2H; 7.80 s and 7.94 s 1H;                        8.01 s and 8.10 s 1H                                                    103   2.31 s 3H; 4.72 s 2H; 4.87 s 2H; 5.44 s 2H; 7.80 s 1H;                        8.10 s 1H                                                               112   3.75 m 4H; 4.15 m 2H; 4.35 m 2H, 5.53 s 2H; 7.83 s 1H;                        8.50 s 1H                                                               113   3.75 m 4H; 4.15 m 2H; 4.38 m 2H; 5.53 s 2H; 7.85 s 1H;                        8.50 s 1H                                                               121   3.75 m 8H; 4.15 m 2H; 4.40 m 2H; 5.35 s 2H; 7.88 s 1H;                        8.38 s 1H                                                               123   3.80 m 8H; 4.15 m 2H; 4.45 m 2H; 5.38 s 2H; 7.88 s 1H;                        8.38 s 1H                                                               124   3.70 m 8H; 4.15 m 2H; 4.30 m 2H; 5.45 s 2H; 7.78 s 1H;                        8.45 s 1H                                                               126   3.80 m 8H; 4.10 m 2H; 4.40 m 2H; 5.60 s 2H; 8.05 s 1H;                        8.70 s 1H                                                               170   3.70 m 8H; 4.00 m 2H; 4.35 m 2H; 5.30 s 2H; 7.75 s 1H;                        8.43 s 1H                                                               171   3.80 m 8H; 4.10 m 2H; 4.45 m 2H; 5.40 s 2H; 7.90 s 1H;                        8.40 s 1H                                                               172   4.60 "t" 2H; 4.80 "t" 2H; 5.40 s 2H;, 7.70 s 1H;                              7.98 s 1H                                                               173   4.65 "t" 2H; 4.85 "t" 2H; 5.40 s 2H;, 7.70 s 1H;                              8.00 s 1H                                                               141   4.20 "t" 2H; 4.45 "t" 2H; 5.21 s 2H; 7.91 s 1H;                               8.13 s 1H                                                               142   4.20 "t" 2H; 4.42 "t" 2H; 5.19 s 2H; 7.90 s 1H;                               8.02 s 1H                                                               145   4.20 "t" 2H; 4.45 "t" 2H; 5.20 s 2H; 7.90 s 1H;                               8.02 s 1H                                                               135   1.8 m 4H; 3.90 "t" 2H; 4.18 "t" 2H; 5.18 s 2H;                                7.89 s 1H; 8.00 s 1H                                                    106   3.7 m 8H; 4.2 m 4H; 5.55 s 2H; 7.87 s 1H; 8.52 s 1 H                    107   3.7 m 8H; 4.2 m 4H; 5.57 s 2H; 7.85 s 1H; 8.50 s 1H                     108   3.7 m 8H; 4.0 m 2H;; 4.45 m 2H; 5.55 s 2H; 7.88 s 1H;                         8.5 s 1H                                                                109   3.7 m 8H; 4.25 m 4H; 5.55 s 2H; 7.85 s 1H; 8.50 s 1H                    110   3.8 m 4H; 4.20 m 4H; 5.45 s 2H; 7.75 s 1H; 8.40 s 1H                    111   3.75 m 4H; 4.05 m 2H; 4.35 m 2H; 5.53 s 2H; 7.83 s 1H;                        8.50 s 1H                                                               178   4.65 "t" 2H; 4.85 "t" 2H; 5.30 s 2H; 7.80 s 1H;                               8.10 s 1H                                                               186   4.30 "t" 2H; 4.65 "t" 2H; 5.22 s 2H; 6.8-7.7 m; 12H                     187   4.20 m 2H; 4.55 m 2H; 5.35 s 2H; 6.08 t 1H;                                   6.6-7.8 m; 1H                                                           197   4.25 "t" 2H; 4.60 "t" 2H; 5.42 s 2H; 7.88 s 1H;                               8.28 s 1H                                                               205   4.25 "t" 2H; 4.55 "t" 2H; 5.32 s 2H; 7.90 s 1H;                               8.28 s 1H.                                                              ______________________________________                                         s = singlet                                                                   "t" = pseudo-triplet                                                          m = multiplet                                                            

The novel compounds may influence virtually all development stages of aplant in different ways, and are therefore employed as growth regulatorsor herbicides.

USE EXAMPLES

I. To determine the growth-regulating properties of the candidatecompounds, soil provided with sufficient nutrients was filled intoplastic pots about 12.5 cm in diameter and summer rape plants weregrowth therein.

The compounds were sprayed onto the plants (post-emergence treatment).The growth-regulating action observed was confirmed at the end of theexperiment by height measurements. The values obtained were comparedwith those for untreated plants.

The compounds used for comparison purposes were active ingredients A andB having the structural formulae given below.

Not only was growth height reduced--the leaves also took on a moreintense color. The increased chlorophyll content is indicative of ahigher rate of photosynthesis, making for bigger yields.

Comparative agents: ##STR7##

The results show that active ingredients 13, 15, 52, 57, 62, 64, 101,103, 116, 117, 119, 121, 122 and 123, applied for example at a rate of1.5 or 6 mg per vessel, reduced growth height to a greater extent (e.g.,68% or 57%) than active ingredients A and B (e.g., 94% and 83%).

II. In the same manner as described under I, summer wheat of the Kalibrivariety (Table 1) and summer barley of the Aramir variety (Table 2) weretreated postemergence. The following results were obtained:

                  TABLE 1                                                         ______________________________________                                        No. of chemical                                                                           mg of active ingre-                                                                           Relative growth                                   example     dient per vessel                                                                              height                                            ______________________________________                                        --          --              100                                               A           1.5             99.2                                                          6               84.8                                              B           1.5             99.5                                                          6               94.0                                              131         1.5             73.2                                                          6               71.6                                              142         1.5             79.2                                                          6               73.2                                              255         1.5             77.4                                                          6               71.9                                              276         1.5             70.1                                                          6               70.1                                              ______________________________________                                    

                  TABLE 2                                                         ______________________________________                                        No. of chemical                                                                           mg of active ingre-                                                                           Relative growth                                   example     dient per vessel                                                                              height                                            ______________________________________                                        --          --              100                                               A           1.5             93.4                                                          6               93.4                                              B           1.5             95.3                                                          6               95.3                                              131         1.5             86.8                                                          6               77.2                                              142         1.5             92.9                                                          6               92.9                                              255         1.5             87.9                                                          6               84.3                                              276         1.5             84.3                                                          6               84.3                                              ______________________________________                                    

The herbicidal action of compounds of the formula I is demonstrated ingreenhouse experiments.

The vessels employed were plastic flowerpots having a volume of 300 cm³,and which were filled with a sandy loam containing about 1.5% humus. Theseeds of the test plants were sown shallow, and separately, according tospecies. For the preemergence treatment, the active ingredients wereapplied to the surface of the soil immediately after the seeds had beensown. The compounds were emulsified or suspended in water as vehicle,and sprayed through finely distributing nozzles. The application rateswere 3.0 and 1.0 kg of active ingredient per hectare. After the agentshad been applied, the vessels were lightly sprinkler-irrigated to inducegermination an growth. Transparent plastic covers were then placed onthe vessels until the plants had taken root. The cover ensured uniformgermination of the plants, insofar as this was not impaired by theactive ingredients.

For the postemergence treatment, the plants were first grown in thevessels to a height of from 3 to 15 cm, depending on growth form, beforebeing treated. The soybean and rice plants were grown in a peat-enrichedsubstrate. For this treatment, either plants which had been sowndirectly in the pots and grown there were selected, or plants which hadbeen grown from seedlings and were transplanted to the pots a few daysbefore treatment. The application rate for postemergence treatment wasfor example 1.0 kg of active ingredient per hectare.

The pots were set up in the greenhouse--species from warmer areas atfrom 20° to 30° C., and species from moderate climates at 15° to 25° C.The experiments were run for 2 to 4 weeks. During this period, theplants were tended and their reactions to the various treatmentsassessed. The scale used for assessment was 0 to 100, 0 denoting nodamage or normal emergence, and 100 denoting nonemergence or completedestruction of at least the visible plant parts.

The plants used in the experiments were Amaranthus spp., Centaureacyanus, Chenopodium album, Echinochloa, crus-galli, Galeopsis spp.,Gaalium aparine, Glycine max., Ipomoea spp., Lamium amplexicaule, Loliummultiflorum, Lycopersicon lycopersicum, Mercurialis annua, Stellariamedia, Triticum aestivum, Viola spp., and Zea mays.

At an application rate of 3.0 kg/ha, compounds nos. 131, 153, 166 and192 had a considerable herbicidal action on broadleaved and grassyplants (postemergence application).

Compound no. 166, applied postemergence at a rate of 0.5 kg/ha, andcompounds nos. 133, 142, 143, 150 and 167 at 1.0 kg/ha are suitable forselectively combatting unwanted plants in crops. Compounds nos. 166 and204 combatted broadleaved weeds at a rate of 2.0 kg/ha.

                                      TABLE 3                                     __________________________________________________________________________    Selective control of broadleaved unwanted plants                              in wheat on postemergence application in the                                  greenhouse                                                                    Com-    Test plants and % damage                                              pound   Triticum*                                                                            Galeopsis                                                                          Lamium                                                                              Mercurialis                                                                         Stellaria                                     no. kg/ha                                                                             aestivum                                                                             spp. ampl. annua media                                         __________________________________________________________________________    166 2.0 0      100  100   100   100                                           204 2.0 0      100  100    98   100                                           __________________________________________________________________________     "Vuka" variety                                                           

We claim:
 1. A process for combatting the growth of unwanted plants,wherein the plants or the soil in which they are located are treatedwith a herbicidally effective amount of an azolylacetophenone ether ofthe formula I ##STR8## where R and R₁ independently of one another areeach hydrogen, halogen, alkyl of 1-5 carbons, cyclohexyl, alkoxy of 1-2carbons, alkylthio of 1-2 carbons, alkylsulfonyl of 1-4 carbons,haloalkyl of 1-4 carbons and 1-5 halogen atoms, nitro, cyano,unsubstituted or substituted phenyl or unsubstituted or substitutedphenoxy, R² is hydrogen or alkyl of 1-4 carbons, R³ is a divalentradical of the formula --(CH₂)_(m) --, --(CH₂ --CH₂ O--)_(u) CH₂ CH₂ --,--(CH₂)CH═CH--(CH₂)-- or --(CH₂)C.tbd.C--(CH₂)--, n, p or uindependently of one another are each 1, 2 or 3, m is an integer from 2to 10 and Az is 1,2,4-triazol-1-yl, pyrazol-1-yl or imidazol-1-yl, ortheir salts or metal complexes.
 2. A process according to claim 1,wherein R and R¹ in formula I independently of one another are fluorine,chlorine, bromine, C₁ -C₅ -alkyl, methoxy, ethoxy, methylthio,ethylthio, C₁ -C₃ -haloalkyl of a maximum of 5 fluorine or chlorineatoms, substituted or unsubstituted phenyl or substituted orunsubstituted phenoxy, R² is hydrogen, R³ is --(CH₂)_(m) --, n and p areeach 1, m is 2, 3 or 4, and Az is 1,2,4-triazol-1-yl.
 3. A processaccording to claim 2, with the proviso that R³ is --(CH₂)_(m) -- and mis
 2. 4. A process for combatting the growth of unwanted plants, whereinthe plants or the soil in which they are located are treated with 0,5 to3 kg/ha of an azolylacetophenone ether herbicide of the formula ##STR9##where R and R₁ independently of one another are each hydrogen, halogen,alkyl of 1-5 carbons, cyclohexyl, alkoxy of 1-2 carbons, alkylthio of1-2 carbons, alkylsulfonyl of 1-4 carbons, haloalkyl of 1-4 carbons and1-5 halogen atoms, nitro, cyano, unsubstituted or substituted phenyl orunsubstituted or substituted phenoxy, R² is hydrogen or alkyl of 1-4carbons, R³ is a divalent radical of the formula --(CH₂)_(m) --, --(CH₂--CH₂ O--)_(u) CH₂ CH₂ --, --(CH₂)CH═CH--(CH₂)-- or--(CH₂)C.tbd.C--(CH₂)--, n, p or u independently of one another are each1, 2 or 3, m is an integer from 2 to 10 and Az is 1,2,4-triazol-1-yl,pyrazol-1-yl or imidazol-1-yl, or their salts or metal complexes.